Thionyl Chloride → HCID 178422743, compound

HRID 1898406Notes

Reaction equation

HRID 1898406 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10]1[NH:11][C:12]2[C:18]3[CH2:19][C:20]([CH3:23])([CH3:22])[O:21][C:17]=3[C:16]([C:24](O)=[O:25])=[CH:15][C:13]=2[N:14]=1.S(Cl)(Cl)=O.[CH:31]1([C:34]2[CH:40]=[CH:39][C:37]([NH2:38])=[CH:36][CH:35]=2)[CH2:33][CH2:32]1.CCN(C(C)C)C(C)C>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10]1[NH:11][C:12]2[C:18]3[CH2:19][C:20]([CH3:23])([CH3:22])[O:21][C:17]=3[C:16]([C:24]([NH:38][C:37]3[CH:39]=[CH:40][C:34]([CH:31]4[CH2:33][CH2:32]4)=[CH:35][CH:36]=3)=[O:25])=[CH:15][C:13]=2[N:14]=1

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 122539274-CyclopropylanilineHCID 178422815HCID 178422815, compound

Product 1

HCID 178422743HCID 178422743, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared following the procedure described for Example-108 using 2-[(2-chloro-6-fluorophenyl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylic acid (Intermediate-15, 0.150 g, 0.399 mmol), thionyl chloride (2.0 mL), 4-cyclopropylaniline (Intermediate-50, 0.079 g, 0.598 mmol), THF (5.0 mL) and DIPEA (2 mL). The obtained crude product was purified by column chromatography on basic alumina eluting with 0.7-1.0% MeOH:DCM to afford 0.045 g of the desired product. 1HNMR (DMSO-d6): δ 0.62-0.63 (m, 2H), 0.90-0.92 (m, 2H), 1.56 (s, 6H), 1.89 (m, 1H), 3.09 (s, 2H), 7.05 (d, J=8.4 Hz, 2H), 7.29-7.47 (m, 4H), 7.54 (d, J=8.4 Hz, 2H), 9.67 (s, 1H), 11.00 (s, 2H); MS [M+H]+: 491.28.

Workup

  1. customThe title compound was prepared
  2. customThe obtained crude product
  3. customwas purified by column chromatography on basic alumina eluting with 0.7-1.0% MeOH

Sources & evidence

ORD record
ord-871372f71d4346cd8f6479a1c8f5483d
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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